The present invention relates to novel 1,2-naphthoquinone-2-diazide-sulfonic acid amides and photosensitive compositions and recording materials containing these compounds.
Many derivatives, in particular aromatic esters, of 1,2-naphthoquinone-2-diazide-sulfonic acids are known for use as photosensitive components in positive-working recording materials. In his book, Light-Sensitive Systems, published by John Wiley and Sons, New York, 1965, pages 343 to 351, Jaromir Kosar describes a number of photosensitive naphthoquinone diazides.
In the customary photosensitive compositions, the naphthoquinone diazides are combined with polymeric binders carrying phenolic hydroxyl groups. These binders are, in general, novolaks, which impart mechanical strength and resistance, but also a certain degree of brittleness, to the layers prepared from the photosensitive compositions.
In order to reduce this brittleness, it is necessary to use a smaller amount of novolaks in the photosensitive compositions or, if possible, to do entirely without novolaks as layer components. This has also the effect that problems which may occur in connection with the mixing or the solubility are obviated.
Monomeric naphthoquinone diazides alone do not form completely homogeneous layers and cannot be considered for use as coating materials. In order to be able to dispense with binders in these photosensitive compositions, polymeric naphthoquinone diazide derivatives must therefore be employed.
A number of polymeric naphthoquinone diazides have already been disclosed, in which the naphthoquinone diazide radical is linked by an ester group to the polymeric basic structure or to correspondingly functionalized side chains of the polymer. For example, DE-C-865 860 and EP-B-0 055 814 describe esters of naphthoquinone diazide sulfonic acids with phenolic resins. Similar compounds are disclosed in JP-A-86/267043, 86/266423, 85/138544 and 87/244039 and in U.S. Pat. No. 4,308,368. JP-A-86/245154 describes reaction products of naphthoquinone diazide sulfonyl chlorides with polyurethanes.
EP-A-0 231 855 describes bis-naphthoquinone diazide sulfonic acid amides of secondary diamines, which are, in particular, sensitive in the medium UV range.
In the above-indicated examples, as far as polymeric compounds are concerned, the naphthoquinone diazide radical is linked to a pre-prepared polymer structure in a polymer-analogous reaction and, in the process, attention must be paid to all known disadvantages of polymer-analogous reactions It is therefore more favorable to couple the incorporation of the naphthoquinone diazide group with the polymerization reaction, i.e., to use appropriate naphthoquinone diazide compounds as monomer units.